Comprehensive Introduction to Methyl 4-(4-oxobutyl)benzoate (CAS 106200-41-3)
Methyl 4-(4-oxobutyl)benzoate, with the CAS number 106200-41-3, is a chemical compound that has gained significant attention in various scientific and industrial fields. This article aims to provide a detailed overview of this compound, including its chemical properties, potential applications, and methods of preparation.
Chemical Properties
Methyl 4-(4-oxobutyl)benzoate is an organic compound with a specific molecular structure. Its chemical formula is C₁₂H₁₄O₃, and it has a molecular weight of approximately 206.24 g/mol. The compound consists of a benzene ring with a methyl ester group (-COOCH₃) attached at the 4 – position and a 4 – oxobutyl side – chain (-CH₂CH₂CH₂CO-) also attached at the 4 – position of the benzene ring.
Physically, it is a solid at room temperature, and its melting and boiling points are characteristic properties that are determined by its molecular structure and intermolecular forces. The solubility of Methyl 4-(4-oxobutyl)benzoate in different solvents is an important aspect. It is soluble in organic solvents such as ethanol, acetone, and dichloromethane. In water, its solubility is relatively low due to the hydrophobic nature of the benzene ring and the long – chain alkyl group.
The compound has certain chemical reactivity. The carbonyl group in the 4 – oxobutyl side – chain can undergo typical carbonyl reactions, such as nucleophilic addition reactions. The ester group can be hydrolyzed under acidic or basic conditions to form the corresponding carboxylic acid and methanol. These chemical properties make it a versatile compound for various chemical transformations.
Applications in Different Fields
Pharmaceutical Industry
In the pharmaceutical industry, Methyl 4-(4-oxobutyl)benzoate can serve as an important intermediate in the synthesis of various drugs. The carbonyl and ester groups in its structure can be modified to introduce other functional groups, which may enhance the biological activity of the final drug product. For example, it can be used in the synthesis of anti – inflammatory drugs. By reacting with specific reagents, the compound can be transformed into derivatives that have the ability to inhibit the production of inflammatory mediators.
It may also be involved in the synthesis of drugs for treating cardiovascular diseases. The side – chain and benzene ring structure can be optimized to interact with specific receptors in the cardiovascular system, thereby regulating blood pressure and lipid metabolism.
Fragrance and Flavor Industry
Methyl 4-(4-oxobutyl)benzoate has a certain odor characteristic. It can be used as a fragrance ingredient in the perfume industry. Its unique chemical structure gives it a delicate and long – lasting scent. It can be blended with other fragrance compounds to create new and complex perfume formulations. In the flavor industry, it can contribute to the development of certain food flavors. Its presence can add a special note to food products, enhancing their overall taste experience.
Materials Science
In materials science, Methyl 4-(4-oxobutyl)benzoate can be used in the synthesis of polymers. By copolymerizing it with other monomers, new polymer materials with specific properties can be obtained. For example, the ester group in the compound can participate in polymerization reactions, and the resulting polymers may have improved mechanical properties, such as increased flexibility and toughness. These polymers can be used in the production of various plastic products, such as packaging materials and engineering plastics.
Preparation Methods
Chemical Synthesis from Starting Materials
One common method for preparing Methyl 4-(4-oxobutyl)benzoate is through a multi – step chemical synthesis starting from simple starting materials. A possible synthesis route involves the reaction of 4 – bromobenzoic acid with methanol to form methyl 4 – bromobenzoate. This reaction is usually carried out in the presence of an acid catalyst, such as sulfuric acid. The reaction equation is as follows: C₇H₅BrO₂+CH₃OH→C₈H₉BrO₂ + H₂O
Then, the methyl 4 – bromobenzoate reacts with a Grignard reagent, such as 4 – oxobutylmagnesium bromide, to form Methyl 4-(4-oxobutyl)benzoate. The Grignard reaction is carried out under anhydrous conditions in an ether solvent, such as diethyl ether or tetrahydrofuran. The reaction mechanism involves the nucleophilic attack of the Grignard reagent on the carbon atom of the carbon – bromine bond in methyl 4 – bromobenzoate.
Biocatalytic Synthesis
Biocatalytic synthesis is an emerging method for preparing Methyl 4-(4-oxobutyl)benzoate. Enzymes can be used to catalyze specific reactions under mild conditions. For example, lipases can be used to catalyze the esterification reaction between 4-(4 – oxobutyl)benzoic acid and methanol. This method has the advantages of high selectivity, mild reaction conditions, and environmental friendliness. However, the efficiency of biocatalytic synthesis may be affected by factors such as enzyme activity, substrate concentration, and reaction temperature.